Ask a Host is our monthly column where we answer frequently asked questions from hoteliers and property managers with practical advice and actionable solutions. Got a challenge or a question of your own? Write to us at hello@smartness.com and you might be featured in the next edition!

Today’s question is:

Response

This is a great question and one that gets right to the heart of a common challenge for hoteliers and property managers alike. Every season, we all invest heavily in acquiring new guests, often paying steep commissions to Booking.com and the like... but then what?

More often than not, we leave the rest to chance. We assume that a great stay will be enough to make guests happy, get a few good reviews, and hopefully have them return next year.

But you’ve already realized something crucial: loyalty doesn’t happen by accident. You need a structured retention strategy to turn new guests into returning ones.

Here’s one way to gauge how urgently you need to invest in loyalty: take a look at what percentage of your bookings come through OTAs. If it’s between 40% and 60%, the need is moderate. If it’s over 70%, it’s definitely time to act.

The main benefit is clear: more direct bookings, lower cost of acquisition (CAC), and drastically reduced OTA commissions.

If you don’t already have a loyalty program in place, and your summer season just ended, here’s your best next step: use the guest contacts you collected this summer and build an email marketing strategy. Here’s how.

Step 1: Organize your database and segment your guests

Start by reviewing all your new bookings from this summer and enrich each guest profile with as much information as possible—beyond just their email address. Were they traveling as a couple or with family? Which country were they coming from? Did they book extras? Were they high spenders or using a promo code? Did they book via your website or an OTA? Was it a last-minute booking or well in advance?

These details will help you identify common traits and group your guests—this is called segmentation. Why segment? Simple: so you can send the right newsletter or offer to the right person at the right time. In short, so you capture their attention without spamming them with generic emails that would go straight to the trash.

If you're using a CRM like Smartconnect, segmentation happens automatically: the software connects to your PMS, imports your guest contacts, and sorts them into segments for you.

For example, as shown below, it may suggest a segment of new guests who stayed between June and today, traveled with family, and came from Germany.

Step 2: Create a communication plan

Once your guests are grouped into segments (or audiences), it’s time to set up a communication plan. This plan should define both the timing and the type of content for your emails. Here are a few examples:

Timing: After check-out

A few days after check-out (or, in your case, you could also send an “end of summer” newsletter once the season ends), schedule your first message to new guests.

This first email should be simple: thank them for their stay and offer a discount code for a future direct booking—valid until a certain date and for a specific time period that you define.

Because you’ve segmented your database, you can tailor this offer for each group. For example:

• Couples: 15% discount for Valentine’s weekend or a “2 nights + romantic dinner” package
• OTA guests: 10% discount with breakfast included, valid only for direct bookings
• Families: 10% discount plus a free service (like free parking or kids under 6 stay free) for Easter stays

With Smartconnect, you can set up this kind of newsletter as an automation—meaning the email will be sent automatically 2 days after check-out (or at your preferred timing) to each specific audience.

Timing: Year-round communication

Throughout the rest of the year, your goal should be to keep the relationship alive with your new guests. But that doesn’t mean sending the usual “Happy Holidays from the team” emails (or at least, not just those). It means sharing thoughtful, customized content.

This approach is called nurturing—you “nurture” your contacts to deepen their connection with your hotel and destination, gradually guiding them toward their next booking. It’s not about promotions, but useful or curiosity-driven content.

Here too, the segmentation you did earlier will help determine what content to send. Here are a few examples:

Families

Christmas: Along with your holiday wishes, send a recipe for a local dessert, including all steps to prepare it with kids.

February/March: Share a guide to the best kid-friendly parks, family beaches, and festivals in your area for summer 2026.

Couples

Christmas: Along with greetings, share a holiday tradition from your region and a recipe for a cozy drink to make together.
April/May: Send a romantic road trip itinerary in your region with a custom playlist created by your staff.

Even though these emails don’t include any special offers, they keep you top of mind and help spark word-of-mouth.

Timing: Low-occupancy periods

If your hotel has periods of historically low occupancy, use your audience segments to send targeted flash offers—valid for just a few days or for specific travel windows.

The goal isn’t broad discounts, but strategic filling of calendar gaps. For example:

• Families: A “kids stay free under 6” promo for your slower spring weekends
• Couples: A “2 nights + free late check-out” package for autumn weekends
• Guests from Germany: A special offer for 5-night stays during a local German holiday like Pentecost

Bonus tip: Focus on extras and experiences!

Loyalty emails don’t always have to focus on discounts or room promotions. Use extras and experiences as your building blocks, and you’ll be able to create a nearly endless variety of unique offers.

Each service becomes a piece you can repurpose—sometimes as a standalone (e.g. “weekend with free bike rental”), other times as part of a seasonal package (e.g. “Easter with local tasting experience”), or as an exclusive perk for direct bookers.

And it doesn’t have to be something you manage in-house. Partner experiences like local tours or excursions can be part of your “toolbox,” too.

This way, you’ll always have fresh ideas to include in your newsletters, without sounding repetitive, and while keeping guests engaged all year round.

Smartconnect is the perfect tool for cutting out the middleman because it brings together all the steps recommended to this hotelier—and automates them. The software segments your contacts into groups and automatically suggests which message to send and to whom.

But that’s not all: thanks to the integrated Marketplace section, you can create your own web page to showcase (and sell) extras and experiences. These are perfect not only as email hooks, but—more importantly—to offer your guests the best possible stay experience, which remains the number one factor for building loyalty.

Want to see it in action?